Issue 17, 2021

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

Abstract

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Graphical abstract: A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

Supplementary files

Article information

Article type
Paper
Submitted
25 6 2021
Accepted
29 7 2021
First published
29 7 2021
This article is Open Access
Creative Commons BY license

Green Chem., 2021,23, 6405-6413

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

A. Jordan, K. D. Whymark, J. Sydenham and H. F. Sneddon, Green Chem., 2021, 23, 6405 DOI: 10.1039/D1GC02251B

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